Problem: Consider the integer\[N = 9 + 99 + 999 + 9999 + \cdots + \underbrace{99\ldots 99}_\text{321 digits}.\]Find the sum of the digits of $N$.

Solution: Let's express the number in terms of $10^n$. We can obtain $(10-1)+(10^2-1)+(10^3-1)+\cdots+(10^{321}-1)$. By the commutative and associative property, we can group it into $(10+10^2+10^3+\cdots+10^{321})-321$. We know the former will yield $1111....10$, so we only have to figure out what the last few digits are. There are currently $321$ 1's. We know the last four digits are $1110$, and that the others will not be affected if we subtract $321$. If we do so, we get that $1110-321=789$. This method will remove three $1$'s, and add a $7$, $8$ and $9$. Therefore, the sum of the digits is $(321-3)+7+8+9=\boxed{342}$.